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Check prices for these dates

Next weekend
Apr 18 - Apr 20
In two weeks
Apr 25 - Apr 27
In one month
May 9 - May 11
In two months
Jun 6 - Jun 8

Compare 26 Condo Rentals in Historic Route 66 with updated reviews, rates, and availability.

Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (91)
"Very clean, good location. "
Stunning 3 BR in prime Chicago location
Visitors Love the Location, I Love the View!
Miscellaneous

Visitors Love the Location, I Love the View!

10.0 out of 10, Exceptional, (404)
"The condo was in a great location. Very comfortable for three people. "
Visitors Love the Location, I Love the View!
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

8.4 out of 10, Very Good, (7)
"Good area clean"
Modern Condo-Obama & University of Chicago Area
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (172)
"Just wanted to be specific, there is a jetted jacuzzi, not a hot tub. So if you and your party are planning for a little hot tub time, this isn't it, however the jetted jacuzzi AND the jetted shower are to die for! I had a wonderful time with my friends here, and had the most relaxing weekend. Thank you so much for a beautiful and restful stay in the most luxury penthouse!"
NEW LUXURY PENTHOUSE CONDO
Left Frame Lofts 210, Where history meets Luxury
Interior

Left Frame Lofts 210, Where history meets Luxury

9.4 out of 10, Exceptional, (28)
"We loved this space! We loved the modern, industrial design It is still under construction, but seems to be close to completion. "
The price is ￥22,896
￥47,156 total
includes taxes & fees
Apr 21 - Apr 22
Left Frame Lofts 210, Where history meets Luxury
Urban Chicago Vacation Rental Condo Near Beach!
Beach nearby

Urban Chicago Vacation Rental Condo Near Beach!

9.0 out of 10, Wonderful, (16)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Urban Chicago Vacation Rental Condo Near Beach!
Experience Chicago living near United Center -
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center -

9.2 out of 10, Wonderful, (24)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center -
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Exterior

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (29)
"The property was exactly as pictured and described. The neighborhood is quiet and we enjoyed walking it and exploring the area. Ola was very responsive and helpful with any questions we had. The beds were SO COMFORTABLE!!! All in all, a great time was had and we would definitely rent this property again. "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Classic Lincoln Park 2 bedroom condo- parking included
Point of interest

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (64)
"I lived in Chicago for years and this was the first time I brought my son. It was exactly what I was hoping for. Walk up in an old building, restaurant on the bottom floor, transit a quick walk away."
Classic Lincoln Park 2 bedroom condo- parking included
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Miscellaneous

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (29)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Perfect location for everything Santa Fe has to offer! Cool air conditioning
Exterior

Perfect location for everything Santa Fe has to offer! Cool air conditioning

9.8 out of 10, Exceptional, (223)
"Excellent property. Everything we needed and great location."
Perfect location for everything Santa Fe has to offer! Cool air conditioning
Charming Santa Fe condo
Fridge, microwave, oven, stovetop

Charming Santa Fe condo

10.0 out of 10, Exceptional, (142)
"The apartment was very comfortable. We lacked for nothing. Very tastefully decorated in southwest decor right down to the silverware. Extremely satisfied overall!"
Charming Santa Fe condo
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (158)
"10/10 recommend! "
NEW LUXURY CONDO WITH PATIO DECK
Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!
Outdoor spa tub

Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!

9.8 out of 10, Exceptional, (54)
"Loved our stay there! The home was perfect and had everything we needed! Perfect communication with property manager. Street is very narrow but manageable! "
Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!
Chic Urban Retreat Near Wrigley Field w/Parking
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (11)
"This was a great home base for our short family getaway to Chicago. Perfect amount of space for family of 4 to crash at the end of each day touristing around Chicago. Very clean. Great communication from hosts. Loved it."
The price is ￥21,600
￥63,821 total
includes taxes & fees
Apr 14 - Apr 15
Chic Urban Retreat Near Wrigley Field w/Parking
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (89)
"Property perfectly located near Wrigley Field, superbly clean and appointed."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
Flagstaff Condo < 1 Mi to Golfing & Hiking!
Fridge, microwave, stovetop, dishwasher

Flagstaff Condo < 1 Mi to Golfing & Hiking!

9.8 out of 10, Exceptional, (47)
"Clean and quiet. Felt like home"
Flagstaff Condo < 1 Mi to Golfing & Hiking!
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Fridge, microwave, oven, stovetop

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

9.0 out of 10, Wonderful, (26)
"Stayed here for my niece's bah mitzvah. There were 6 of us and it was the perfect size."
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Historic Route 66

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (726)
"Great family place to stay. "
The price is ￥15,790
￥22,762 total
includes taxes & fees
Apr 14 - Apr 15
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (465)
"Great location to restaurants, grocery and easy to get to convention center or downtown"
The price is ￥15,821
￥18,572 total
includes taxes & fees
Apr 16 - Apr 17
Sonder South Wabash
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2036)
"The first room they gave us had a smell when we first entered. Upon inspection the garbage disposal was broken and had a foul smell. We contacted the front desk who sent the maintenance person who confirmed it was broken and emitted a foul smell. They apologized and provided us a different room which was completely remodeled. It was so nice, we wish we found this place for the two prior nights we stayed in Sedona!"
The price is ￥33,696
￥38,717 total
includes taxes & fees
May 12 - May 13
Junipine Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.